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The Worst Days in a Founder/CEO’s Professional Life

People often ask me how things are going at BloomReach. I pretty much give the same stock answer that any halfway decent CEO does – “It’s going great. Awesome. Couldn’t be better.” Of course deep down, there are always the dark days. And in those dark days, it helps to know you’re not alone – that people have been through it before you and that others will go through it after you. I’m talking about successful businesses here, because there are really only two ways to be unsuccessful in a startup: quit or run out of money. Quitting as a founder is like leaving your child to be raised by others. Sometimes there are good reasons to do it, but not very many and you’ll spend most of the rest of your life explaining why you did. Running out of money, after you’ve exhausted all of your options means the inevitable – you’re laying off people, calling it a learning experience and moving on with life. It goes without saying that either of those scenarios are almost always more devastating than any of the below. But there are a lot of bad days in really good companies. Figuring out how to handle them effectively is the key to long-term emotional stability. Here are some of the worst:

Great people leave you: Starting and building a company is an inherently emotional experience. You build your enterprise with a group of brothers and sisters. You aim to have their personal success intertwined with the company’s success. You invest in them and they invest in your shared journey. And then (for all kinds of reasons), they choose to leave. You fight to keep them (as you should) but don’t succeed. You can feel a sense of betrayal or dismay. Let it go. Have confidence that the business you have built will attract other great people. If you’ve done things right, the paradox is that every great person can have an immense impact and yet, the business will thrive even without them. Have them leave on great terms – always as ambassadors of your business.

Macro events start impacting your business: You built a great business and yet forces beyond your control are negatively impacting it. Maybe Apple came out with a competitive product. Maybe Facebook released a feature that kills your distribution channel. Maybe the financial markets are shut down for further investment. It’s rough. There is absolutely nothing you can do. The temptation is to just hope it gets better or you somehow survive the macro tsunami. Unfortunately, delaying just makes things worse. The right answer is to fully absorb the state of the world and ask the question: “If a new CEO walked in today what would he/she do?” Whatever that is, do it.

You lose a big deal or a big customer leaves you: You did everything right. You built and sold a killer product. You engaged the right buyers and delivered a value proposition that was tremendous. You built the right relationships. And then you lose a deal – maybe to a competitor, maybe to a stalled budgeting cycle, maybe for reasons you don’t understand. Once again, you fought hard to keep them but did not succeed. Take a deep breath and analyze the situation. What could you have done better or differently? Sometimes, the genuine answer is “not much.” Make sure there is nothing systemic going on; part on good terms and move on.

There are many more challenges that can be more business-impacting (lack of product/market fit or inability to scale for example). However, you don’t feel quite as powerless in those situations as the ones above- there is always a way forward and you can usually explain the challenges you face. Interestingly, it’s exactly the characteristics of founder/leaders that make the above three situations particularly rough. For founders, everything is personal. The product is personal. The team is personal. Customer wins are personal. That is what can make founder-led businesses special. And it is also what makes the dark days darker. On those dark days, try hard not to respond in the moment with an email or a tirade that you will later regret. Try hard not to take it out on your loved ones. Just for those days, be a professional manager, not a founder.